Trump has personally helped Tyson and they're "friends" so I think he's compromised in that regard. I don't think his support back in the day was pretend or just edge though.

I think like a lot of boomers he's just aged and reached a point where he just chooses comfort over anything that might resemble struggle. Some of this misjudgement might also be coming from experiences when he was younger too, given that he says he's known him in personal capacity since he was 19 or 20 years old.